Trump declared a $916 million loss on his tax returns in 1995—a deduction "so substantial it could have allowed him to legally avoid paying any federal income taxes for up to 18 years," according to the Times.

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Tax experts told The Times that after several epically failed business ventures in the early 1990s—including "mismanagement of three Atlantic City casinos, his ill-fated foray into the airline business, and his ill-timed purchase of the Plaza Hotel in Manhattan"—he could have potentially used that massive loss to cancel out "an equivalent amount of taxable income over an 18-year-period":

"Although Mr. Trump's taxable income in subsequent years is as yet unknown, a $916 million loss in 1995 would have been large enough to wipe out more than $50 million a year in taxable income over 18 years."

The loss could have eliminated federal income taxes that Trump would have otherwise had to pay for the money he made from The Apprentice and the $45 million he was paid from the publicly traded company created "to assume ownership of his troubled Atlantic City casinos."

"He has a vast benefit from his destruction," assistant professor at New York University's Schack Institute of Real Estate Joel Rosenfield told the Times. "Do you realize you can create $916 million in income without paying a nickel in taxes?"

The Times also approached Jack Mitnick, Trump's accountant for over 30 years, who said that "[Trump] knew we could use the tax code to protect him":

"Mr. Mitnick...said there were times when even he, for all his years helping wealthy New Yorkers navigate the tax code, found it difficult to face the incongruity of his work for Mr. Trump. He felt keenly aware that Mr. Trump was living a life of unimaginable luxury thanks in part to Mr. Mitnick's ability to relieve him of the burden of paying taxes like everyone else."

Though Trump declined to comment, the campaign released a relatively vague statement about the claims:

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"Mr. Trump is a highly-skilled businessman who has a fiduciary responsibility to his business, his family and his employees to pay no more tax than legally required. That being said, Mr. Trump has paid hundreds of millions of dollars in property taxes, sales and excise taxes, real estate taxes, city taxes, state taxes, employee taxes and federal taxes. Mr. Trump knows the tax code far better than anyone who has ever run for President and he is the only one that knows how to fix it."